Oak Street Health

HQ
Chicago
Total Offices: 13
3,000 Total Employees
Year Founded: 2012

Oak Street Health Compensation & Benefits in Chicago

Updated on September 08, 2026

This page summarizes recurring themes identified from responses generated by popular LLMs to common candidate questions about Oak Street Health and has not been reviewed or approved by Oak Street Health.

How are the compensation & benefits at Oak Street Health?

Strengths in health coverage breadth, retirement support, and everyday wellbeing perks are accompanied by concerns about plan costs and the generosity of time off during CVS integration. Together, these dynamics suggest the Chicago office experiences a broad, standardized package whose on‑the‑ground value hinges on medical cost-sharing and how PTO policies apply to specific roles.

Key Insight for Candidates

In Chicago, employees consistently perceive Oak Street Health’s perks and benefits as below many local peers, despite access to CVS Health’s broad package (Aetna coverage, strong 401(k) match, retail discounts). For candidates, the breadth is there, but overall value may feel less competitive in the Chicago market.

Positive Themes About Oak Street Health

  • Healthcare Strength: In Chicago, colleagues benefit from CVS‑aligned Aetna medical, dental, and vision coverage with virtual care and no‑cost preventive and MinuteClinic wellness services. Feedback suggests this large‑employer platform is viewed as solid overall.
  • Retirement Support: In Chicago, the retirement offering includes a competitive 401(k) company match alongside access to an employee stock purchase plan. Feedback suggests the post‑integration match is a standout component of total rewards.
  • Wellbeing & Lifestyle Benefits: Chicago teams have access to no‑cost confidential counseling through the EAP, fitness discounts, and meaningful CVS retail discounts. These extras are often cited as adding everyday value alongside core insurance.

Considerations About Oak Street Health

  • High Benefits Costs: Health coverage costs in Chicago are sometimes described as higher after the CVS integration, particularly premiums and deductibles. This perception tempers otherwise favorable views of the plan’s breadth.
  • Limited Leave & Time Off: Time off in Chicago is portrayed as modest in certain roles, with limited sick time and variable holiday counts noted during integration. These constraints can make PTO feel tight even as other benefits expand.
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These insights are generated using AI and may not reflect internal data or verified company information. They are intended solely for general informational purposes and should not be considered a definitive assessment of the company’s reputation. If you are a representative of this company, and would like this page to be removed, you may contact us via this form.
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